HERBICIDAL COMPOSITIONS BASED ON 3-PHENYLURACILS AND N-[[4-[(CYCLOPROPYLAMINO)-CARBONYL]PHENYL]SULFONYL]-2-METHOXYBENZAMIDE

Abstract

A herbicidal composition comprising 3-phenyluracils I wherein R1 to R7 are as defined in the specification and N-[[4-[(cyclopropylamino)carbonyl]phenyl]sulfonyl]-2-methoxybenzamide II and optionally at least one herbicide selected from a group as defined in the specification.

Full Text

The present invention relates to herbicidally active compositions comprising 3-
phenyluracils I, N-[[4-[(cyclopropylamino)carbonyl]phenyl]sulfonyl]-2-
methoxybenzamide II and optionally at least one further herbicide III.
In crop protection products, it is desirable in principle to increase the specificity and the
reliability of the action of active compounds. In particular, it is desirable for the crop
protection product to control the harmful plants effectively and, at the same time, to be
tolerated by the useful plants in question. It is known that in some cases better crop
plant compatibility can be achieved by joint application of specifically acting herbicides
with organic active compounds, which act as antidotes or antagonists. Owing to the
fact that they can reduce or even prevent damage to the crop plants, they are also re-
ferred to as safeners.
3-phenyluracils I and compositions comprising 3-phenyluracils I are known as highly
effective herbicides (e.g. WO 01/83459, WO 03/24221, WO 04/80183). However, their
compatibility with dicotyledonous crop plants such as cotton, oilseed rape, flax, lentil,
sugar beet, tobacco, sunflowers and soybeans and some graminaceous plants such as
oat, barley, millet, corn, rice, wheat and sugar cane is not always satisfactory, i. e. in
addition-to the harmful plants, the crop plants are also damaged to an extent which is
not acceptable. It is possible to spare the useful plants by lowering the application
rates; however the extent of the control of harmful plants is naturally also reduced.
Therefore it is an object of the present invention to improve the crop-plant compatibility
of 3-phenyluracils I, optionally in the presence of further herbicides III.
Surprisingly it has now been found that compositions comprising at least one 3-
phenyluracil I or its agriculturally acceptable salts, N-[[4-[(cyclopropylamino)carbonyl]-
phenyl]sulfonyl]-2-methoxybenzamide II or its agriculturally acceptable salts; and op-
tionally at least one further herbicide III, improve the crop-plant compatibility of 3-
phenyluracils I.
N-[[4-[(cyclopropylamino)carbonyl]phenyl]sulfonyl]-2-methoxybenzamide II (CAS no.
221667-31-8)

is a safener, which is disclosed, for example, in WO 99/16744 and WO 05/00797.

including its agriculturally acceptable salts;
and optionally at least one herbicide III selected from the following classes III.1) to
III.15):

III.1) lipid biosynthesis inhibitors;
III.2) acetolactate synthase inhibitors (ALS inhibitors);
III.3) photosynthesis inhibitors;
III.4) protoporphyrinogen-IX oxidase inhibitors;
III.5) bleacher herbicides;
III.6) enolpyruvyl shikimate 3-phosphate synthase inhibitors (EPSP inhibitors);
III.7) glutamine synthetase inhibitors;
III.8) 7,8-dihydropteroate synthase inhibitors (DHP inhibitors);
III.9) mitose inhibitors;
III.10) inhibitors of the synthesis of long chain fatty acids (VLCFA inhibitors);
III.11) cellulose biosynthesis inhibitors;
III.12) decoupler herbicides;
III.13) auxin herbicides;
III.14) auxin transport inhibitors;
III.15) other herbicides selected from the group consisting of benzoylprop, flam-
prop, flamprop-M, bromobutide, chlorflurenol, cinmethylin, methyldy-
muron, etobenzanid, fosamine, metam, pyributicarb, oxaziclomefone,
dazomet, triaziflam and methyl bromide;
including their agriculturally acceptable salts and, provided they have a carboxyl
group, their agriculturally acceptable derivatives.
The invention relates in particular to compositions in the form of safened herbicidally
active crop protection compositions comprising a herbicidally effective amount of at
least one composition of 3-phenyluracil I with N-[[4-[(cyclopropylamino)carbonyl]-
phenyl]sulfonyl]-2-methoxybenzamide II and optionally at least one herbicide III, as
defined above, and at least one inert liquid and/or solid carrier, if desired at least one or
more surfactants and, if appropriate, at least one or more further auxiliaries customary
for crop protection compositions.
The invention also relates to compositions in the form of a crop protection composition
formulated as a 2-component composition comprising
a first component, which comprises the 3-phenyluracil I and the N-[[4-[(cyclopropyl-
amino)carbonyl]phenyl]sulfonyl]-2-methoxybenzamide II, a solid or liquid carrier and, if
appropriate, one or more surfactants, and
a second component, which comprises at least one further herbicide III and optionally
the N-[[4-[(cyclopropylamino)carbonyl]phenyl]sulfonyl]-2-methoxybenzamide II, a solid
or liquid carrier and, if appropriate, one or more surfactants,
where both components may additionally comprise further auxiliaries customary for
crop protection compositions.

The invention also relates to compositions in the form of a crop protection composition
formulated as a 2-compbnent composition comprising
a first component, which comprises the 3-phenyluracil I and optionally the N-[[4-
[(cyclopropylamino)carbonyl]phenyl]sulfonyl]-2-methoxybenzamide II, a solid or liquid
carrier and, if appropriate, one or more surfactants, and
a second component, which comprises at least one further herbicide III and the N-[[4-
[(cyclopropylamino)carbonyl]phenyl]sulfonyl]-2-methoxybenzamide II, a solid or liquid
carrier and, if appropriate, one or more surfactants,
where both components may additionally comprise further auxiliaries customary for
crop protection compositions.
The invention furthermore relates to a method for controlling undesired vegetation,
which comprises allowing a herbicidally effective amount of a composition according to
the present invention to act on plants, their habitat or on seed.
The invention furthermore relates to a method for controlling undesired vegetation,
which comprises applying a herbicidal composition according to the present invention
before, during and/or after the emergence of the undesirable plants, the components I,
II and optionally III being applied simultaneously or in succession.
The invention furthermore relates to a method for controlling undesirable vegetation in
crops, in particular in crops of oat, barley, millet, corn, rice, wheat, sugar cane, cotton,
oilseed rape, flax, lentil, sugar beet, tobacco, sunflowers and soybeans or in perennial
crops.
The invention furthermore relates to a method for controlling undesirable vegetation in
crops which, by genetic engineering or by breeding, are resistant to one or more herbi-
cides and/ or fungicides and/or or to attack by insects.
The invention furthermore relates to a method of safening the phytotoxic activity of a 3-
phenyluracil I, or an agriculturally acceptable salt thereof, according to the present
ivention on crops;
preferably crops selected from oat, barley, millet, corn, rice, wheat, sugar cane,
cotton, oilseed rape, flax, lentil, sugar beet, tobacco, sunflowers, soybeans, rye,
triticale, potato, peas, beans, sorghum, grapes, citrus, apple and almond;
especially preferred crops selected from oat, barley, millet, corn, rice, wheat,
sugar cane, cotton, oilseed rape, flax, lentil, sugar beet, tobacco, sunflowers and
soybeans;
which comprises applying said 3-phenyluracil I, or an agriculturally acceptable salt
thereof, in combination with N-[[4-[(cyclopropylamino)carbonyl]phenyl]sulfonyl]-2-
methoxybenzamide of formula II or an agriculturally acceptable salt thereof;

C3-C7-cycloalkyl: a monocyclic saturated hydrocarbon.ring having 3 to 7 ring
members, such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl or cycloheptyl;
C3-C7-cycloalkenyl: monocyclic unsaturated hydrocarbon ring having 3 to 7 ring
members, such as cycloprop-1-enyl, cycloprop-2-enyl, cyclobut-1-enyl, cyclobut-
2-enyl, cyclobut-1,3-dienyl, cyclopent-1-enyl, cyclopent-2-enyl, cyclopent-3-enyl,
cyclopent-2,4-dienyl, cyclohex-1-enyl, cyclohex-2-enyl, cyclohex-3-enyl; cyclo-
hex-1,3-dienyl, cyclohex-1,5-dienyl, cyclohex-2,4-dienyl, or cyclohex-2,5-dienyl.
If the phenyluracils I and/or the herbicides III are capable of forming geometrical iso-
mers, for example E/Z isomers, it is possible to use both the pure isomers and compo-
sitions thereof in the compositions according to the invention. If the phenyluracils I
and/or the herbicides ill have one or more centers of chirality and, as a consequence,
are present as enantiomers or diastereomers, it is possible to use both the pure enan-
tiomers and diastereomers and their compositions in the compositions according to the
invention.
If the phenyluracils and/or the herbicides III have functional groups, which can be ion-
ized, they can also be used in the form of their agriculturally acceptable salts. Also, N-
[[4-[(cyclopropylamino)carbonyl]phenyl]sulfonyl]-2-methoxybenzamide can be used in
the form of its agriculturally acceptable salts. In general, the salts of those cations or
anions are suitable whose cations or anions have no adverse effect on the action of the
active compounds ("agricultural acceptable").
Preferred cations are the ions of the alkali metals, preferably of lithium, sodium and
potassium, of the alkaline earth metals, preferably of calcium and magnesium, and of
the transition metals, preferably of manganese, copper, zinc and iron, furthermore am-
monium and substituted ammonium in which one to four hydrogen atoms are replaced
by C1-C4-alkyl, hydroxy-C1-C4-alkyl, C1-C4-alkoxy-C1-C4-alkyl, hydroxy-C1-C4-alkoxy-C1-
C4-alkyl, phenyl or benzyl, preferably ammonium, methylammonium, isopropylammo-
nium, dimethylammonium, diisopropylammonium, trimethylammonium, tetramethyl-
ammonium, tetraethylammonium, tetrabutylammonium, 2-hydroxyethylammonium, 2-
(2-hydroxyethoxy)eth-1-ylammonium, di(2-hydroxyeth-1-yl)ammonium, benzyl-
trimethylammonium, benzyltriethylammonium, furthermore phosphonium ions, sulfo-
nium ions, preferably tri(C1-C4-alkyl)sulfonium such as trimethylsulfonium, and sul-
foxonium ions, preferably tri(C1-C4-alkyl)sulfoxonium.
It is possible to use the phenyluracils of the formula I, the safener N-[[4-
[(cyclopropylamino)carbonyl]phenyl]sulfonyl]-2-methoxybenzamide II, and optionally at
least one herbicide III selected from chlorazifop, clodinafop, clofop, cyhalofop, diclofop,
fenoxaprop, fenoxaprop-P, fenthiaprop, fluazifop; fluazifop-P, haloxyfop, haloxyfop-P,

R2 is trifluoromethyl;
R3 is fluorine;
R4 is chlorine;
R5 is hydrogen;
R6, R7 independently of one another are C1-C6-alkyl.
In another particularly preferred embodiment of the invention, the compositions com-
prise at least one 3-phenyluracil I in which the variables R1 to R7 in formula I have the
meanings below (hereinbelow also referred to as 3-phenyluracils lb):
R1 is NH2;
R2 is trifluoromethyl;
R3 is fluorine;
R4 is chlorine;
R5 is hydrogen;
R6, R7 independently of one another are C1-C6-alkyl.
Particularly preferred herbicides I are 3-phenyluracils 1.1, especially preferred 3-
phenyluracils 1.1.1 to 1.1.74, listed below in table 1, wherein R1, R6 and R7 have the
meanings given in table 1:

In an especially preferred embodiment of the invention, the compositions comprise 3-
phenyluracil 1.1.7.
Among those compositions according to the present invention, preference is given to
those which comprise at least one herbicide III selected from groups III.1 to III. 7, III.9
to III.11,III.13,III.14 and III.15; preferably in combination with a 3-phenyluracil la or lb.
Among those compositions according to the present invention, preference is given to
those which comprise at least one herbicide III selected from groups III.1,III.2,III.3,
III.5, III.6, III.7, III.9,III.10,III.13, III.14 and III.15;
in particular selected from groups III.1, III.2, III.3, III.5,III.13 and III.15;
preferably in combination with a 3-phenyluracil la or lb.
Preferred herbicides of groups III.1) to III.15) are the compounds listed below:
III.1) from the group of the lipid biosynthesis inhibitors:

III.5) from the group of the bleacher herbicides:
norflurazon, diflufenican, picolinafen, beflubutamid, mesotrione, sulcotrione,
isoxaflutole, benzofenap, pyrazolynate, pyrazoxyfen, benzobicyclon, 4-(3-
trifluoromethylphenoxy)-2-(4-trifluoromethylphenyl)pyrimidine, topramezone, 4-
hydroxy-3-{[2-methyl-6-(trifluoromethyl)-3-pyridinyi]carbony4}bicyclo[3.2.1]oct-3-
en-2-one, 4-hydroxy-3-{[2-(2-methoxyethoxy)methyl-6-(trrfluoro-methyl)-3-
pyridinyl]carbonyl}bicylo[3.2.1]oct-3-en-2-one, 4-hydroxy-3-[4-(methylsulfonyl)-2-
nitrobenzoyl]bicyclo[3.2.1]-oct-3-en-2-one, 2-[2-chloro-4-(methylsulfonyl)-3-
[(2,2,2-trifluoroethoxy)methyl]benzoyl]-3-hydroxy-2-cyclohexen-1-oneand
pyrasulfotole;
III.6) from the group of the EPSP synthase inhibitors:
glyphosate;
III.7) from the group of the glutamine synthase inhibitors:
glufosinate;
III.9) from the group of the mitose inhibitors:
oryzalin, pendimethalin and trifluralin;
III.10) from the group of the VLCFA inhibitors:
acetochlor, butachlor, dimethenamid, dimethenamiC1-P, metazachlor,
metolachlor, S-metolachlor, pethoxamid, pretilachlor, flufenacet, mefenacet,
fentrazamide, cafenstrole and indanofan;
III.13) from the group of the auxin herbicides:
2,4-D, dichlorprop, dichlorprop-P, mecoprop, MCPA, mecoprop-P, dicamba,
quinclorac, quinmerac, clopyralid, fluroxypyr, picloram, triclopyr and
aminopyralid;
III.14) from the group of the auxin transport inhibitors:
diflufenzopyr;
lll.15)cinmethylin, oxaziclomefone and triaziflam;
and the agriculturally acceptable salts and the agriculturally acceptable derivatives of
these herbicides, provided they have a carboxyl group.
The categorization of the herbicides III according to their mode of action is based on
current understanding. If a herbicide acts by more than one mode of action, this sub-
stance was assigned to only one mode of action.

Particular preference is given to those binary and ternary compositions which comprise
at least one 3-phenyluracil I and N-[[4-[(cyclopropylamino)carbonyl]phenyl]sulfonyl]-2-
methoxybenzamide II and, if appropriate, one or more herbicides III.
Here and below, the term "binary compositions" includes compositions which comprise
one or more (for example 2 or 3) 3-phenyluracils I and N-[[4-[(cyclopropylamino)-
carbonyl]phenyl]sulfonyl]-2-methoxybenzamide II.
Correspondingly, the term "ternary compositions" includes compositions which com-
prise one or more (for example 2 or 3) 3-phenyluracils I, N-[[4-[(cyclopropylamino)-
carbonyl]phenyl]sulfonyl]-2-methoxybenzamide II, and one or more (for example 2 or 3)
herbicides III.
In binary compositions the weight ratio of the active compounds I: II is usually in the
range from 1:10 to 10:1, preferably in the range from 1:5 to 5:1, in particular in the
range from 1:3 to 3:1.
In ternary compositions which comprise both a 3-phenyluracil I, N-[[4-[(cyclopropyl-
amino)carbonyl]phenyl]sulfonyl]-2-methoxybenzamide II and at least one herbicide III,
the relative weight ratios of the components I: II: III are usually in the range from
10:1:1 to 1:10:20, preferably from 5:1:1 to 1:5:10, in particular from 3:1:1 to 1:3:5.
In these ternary compositions, the weight ratio of N-[[4-[(cyclopropylamino)carbonyl]-
phenyl]sulfonyl]-2-methoxybenzamide II to herbicide III is preferably in the range from
10:1 to 1:20.
In a particularly preferred embodiment of the invention, preference is given to those
compositions of the invention which comprise a 3-phenyluracil I, especially la or lb, in
combination with N-[[4-[(cyclopropylamino)carbonyl]phenyl]sulfonyl]-2-methoxy-
benzamide II.
Preference is also given to those compositions of the invention comprising as the only
herbicidal active compound a 3-phenyluracil I,
preferably phenyluracil la or lb,
particularly preferred phenyluracil I selected from the group consisting of 3-
phenyluracils 1.1.1 to 1.1.74,
especially preferred 3-phenyluracil 1.1.7,
in combination with the safener N-[[4-[(cyclopropylamino)carbonyl]phenyl]sulfonyl]-2-
methoxybenzamide II.

Preference is also given to those compossitions of the invention comprising as the only
herbicidal active compound phenyluracil la in combination with the safener N-[[4-
[(cyclopropylamino)carbonyl]phenyl]sulfonyl]-2-methoxybenzamide II.
Furthermore preference is given to those compositions of the invention comprising a 3-
phenyiuracil I,
preferably phenyluracil la or lb,
particularly preferred phenyluracil I selected from the group consisting of 3-
phenyluracils 1.1.1 to 1.1.74,
especially preferred 3-pheny!uracil 1.1.7,
in combination with N-[[4-[(cyclopropylamino)carbonyl]phenyl]sulfonyl]-2-
methoxybenzamide II, and
at least one, especially exactly one, herbicide III selected from the classes III.1) to
III.15).
Preference is also given to those compositions of the invention comprising 3-
phenyluracil la, in combination with N-[[4-[(cyclopropylamino)carbonyl]phenyl]sulfonyl]-
2-methoxybenzamide II and at least one, especially exactly one, herbicide III selected
from the classes III.1) to III.15).
In another particularly preferred embodiment of the invention, preference is given to
those compositions of the invention which comprise a 3-phenyluracil I, especially la or
lb, preferably phenyluracil la, particularly preferred phenyluracil 1.1.7, in combination
with N-[[4-[(cyclopropylamino)carbonyl]phenyl]sulfonyl]-2-methoxybenzamide II, and at
least one, especially exactly one, herbicidally active compound of the group III.1), in
particular selected from the group consisting of clodinafop, cyhalofop, diclofop,
fenoxaprop, fenoxaprop-p, fluazifop, fluazifop-P, haloxyfop, haloxyfop-P, metamifop,
quizalofop, quizalofop-P, alloxydim, butroxydim, clethodim, cloproxydim, cycloxydim,
profoxydim, sethoxydim, tepraloxydim, tralkoxydim and pinoxaden.
In another particularly preferred embodiment of the invention, preference is given to
those compositions of the invention which comprise a 3-phenyluracil I, especially la or
lb, preferably phenyluracil la, particularly preferred phenyluracil 1.1.7, in combination
with N-[[4-[(cyclopropylamino)carbonyl]phenyl]sulfonyl]-2-methoxybenzamide II, and at
least one, especially exactly one, herbicidally active compound of the group III.2), in
particular selected from the group consisting of amidosulfuron, bensulfuron, chlori-
muron, chlorsulfuron, cyclosulfamuron, flupyrsulfuron, foramsulfuron, halosulfuron,
imazosulfuron, iodosulfuron, mesosulfuron, metsulfuron, nicosulfuron, oxasulfuron,
primisulfuron, prosulfuron, pyrazosulfuron, rimsulfuron, sulfometuron, sulfosulfuron,
thifensulfuron, triasulfuron, tribenuron, trifloxysulfuron, triflusulfuron, tritosulfuron, ima-
zamethabenz, imazamox, imazapic, imazapyr, imazaquin, imazethapyr, cloransulam,

trifluoroethoxy)methyl]ben2oyl]-3-hydroxy-2-cyclohexen-1 -one and pyrasulfotole. ^ -
In another particularly preferred embodiment of the invention, preference is given to
those compositions of the invention which comprise a 3-phenyluracil I, especially la or
lb, preferably phenyluracil la, particularly preferred phenyluracil 1.1.7, in combination
with N-[[4-[(cyclopropylamino)carbonyl]phenyl]sulfonyl]-2-methoxybenzamide II, and at
least one, especially exactly one, herbicidally active compound of the group III.6), in
particular glyphosate.
In another particularly preferred embodiment of the invention, preference is given to
those compositions of the invention which comprise a 3-phenyluracil I, especially la or
lb, preferably phenyluracil la, particularly preferred phenyluracil 1.1.7, in combination
with N-[[4-[(cyclopropylamino)carbonyl]phenyl]sulfonyl]-2-methoxybenzamide II, and at
least one, especially exactly one, herbicidally active compound of the group III.7), in
particular glufosinate.
In another particularly preferred embodiment of the invention, preference is given to
those compositions of the invention which comprise a 3-phenyluracil I, especially la or
lb, preferably phenyluracil la, particularly preferred phenyluracil 1.1.7, in combination
with N-[[4-[(cydopropylamino)carbonyl]phenyl]sulfonyl]-2-methoxybenzamide II, and at
least one, especially exactly one, herbicidally active compound of the group III.9), in
particular oryzalin, pendimethalin and trifluralin.
In another particularly preferred embodiment of the invention, preference is given to
those compositions of the invention which comprise a 3-phenyluracil I, especially la or
lb, preferably phenyluracil la, particularly preferred phenyluracil 1.1.7, in combination
with N-[[4-[(cyclopropylamino)carbonyl]phenyl]sulfonyl]-2-methoxybenzamide II, and at
least one, especially exactly one, herbicidally active compound of the group III.10), in
particular selected from the group consisting of acetochlor, butachlor, dimethenamid,
dimethenamiC1-P, metazachlor, metolachlor, S-metolachlor, pethoxamid, pretilachlor,
flufenacet, mefenacet, fentrazamide, cafenstrole and indanofan.
In another particularly preferred embodiment of the invention, preference is given to
those compositions of the invention which comprise a 3-phenyluracil I, especially la or
lb, preferably phenyluracil la, particularly preferred phenyluracil 1.1.7, in combination
with N-[[4-[(cyclopropylamino)carbonyl]phenyl]sulfonyl]-2-methoxybenzamide II, and at
least one, especially exactly one, herbicidally active compound of the group-1H.13), in
particular selected from the group consisting of 2,4-D, dichlorprop, dichlorprop-P, me-
coprop, MCPA, mecoprop-P, dicamba, quinclorac, quinmerac, clopyralid, fluroxypyr,
picloram, triclopyr and aminopyralid.

In another particularly preferred embodiment of the invention, preference is given to
those compositions of the invention which comprise a 3-phenyluracil I, especially la or
lb, preferably phenyluracil la, particularly preferred phenyluracil 1.1.7, in combination
with N-[[4-[(cyclopropylamino)carbonyl]phenyl]sulfonyl]-2-methoxybenzamide II, and at
least one, especially exactly one, herbicidally active compound of the group III.14), in
particular diflufenzopyr.
In another particularly preferred embodiment of the invention, preference is given to
those compositions of the invention which comprise a 3-phenyluracil I, especially la or
lb, preferably phenyluracil la, particularly preferred phenyluracil 1.1.7, in combination
with N-[[4-[(cyclopropylamino)carbonyl]phenyl]sulfonyl]-2-methoxybenzamide II, and at
least one, especially exactly one, herbicidally active compound of the group III.15), in
particular selected from the group consisting of cinmethylin, oxaziclomefone and tri-
aziflam.
In the preferred or especially preferred compositions described above the 3-phenyl-
uracils I, N-[[4-[(cyclopropylamino)carbonyl]phenyl]sulfonyl]-2-methoxybenzamide II,
and the herbicides III can be used in the form of their agriculturally acceptable salts or
in the form of an agriculturally acceptable derivative thereof as described above.
The weight ratios of the individual components in the compositions are within the limits
stated above.
Among the especially preferred compositions, particular preference is given to those
compositions of the invention wherein the variables R1 to R7 have the preferred mean-
ings, especially the particularly preferred meanings. Particular preference is given to 3-
phenyluracils la and lb, very particular to 3-phenyluracils 1.1.1 to 1.1.74, as defined
above.
Also particular preference is given to 3-phenyluracils la, especially to 3-phenyluracil
1.1.7, as defined above.
Preference is also given, for example, to those compositions which comprise, as active
compound I, the phenyluracil 1.1.1 and, as further active compound, the safener N-[[4-
[(cyclopropylamino)carbonyl]phenyl]sulfonyl]-2-methoxybenzamide II and, as further
active compound, the substances listed in one row of table 2 (compositions 1.1 to
1.173).
The weight ratios of the individual components in the compositions 1.1 to 1.173 are
within the stated limits, in the case of binary compositions of phenyluracil 1.1.1 and N-
[[4-[(cyclopropylamino)carbonyl]phenyl]sulfonyl]-2-methoxybenzamide II for example
1:1, and in the case of ternary compositions of phenyluracil hi ;1, N-[[4-

Preference is also given to the compositions 2.1 - 2.173, which differ from the corre-
sponding compositions 1.1 -1.173 only in that the phenyluracil 1.1.1 is replaced by the
phenyluracil 1.1.2.
Preference is also given to the compositions 3.1 - 3.173, which differ from the corre-
sponding compositions 1.1 - 1.173 only in that the phenyluracil 1.1.1 is replaced by the
phenyluracil 1.1.3.
Preference is also given to the compositions 4.1 - 4.173, which differ from the corre-
sponding compositions 1.1 - 1.173 only in that the phenyluracil 1.1.1 is replaced by the
phenyluracil 1.1.4.
Preference is also given to the compositions 5.1 - 5.173, which differ from the corre-
sponding compositions 1.1 - 1.173 only in that the phenyluracil 1.1.1 is replaced by the
phenyluracil 1.1.5.

Preference Is-also given to the compositions 6.1 - 6.173, which "differ from the corre-
sponding compositions 1.1 - 1.173 only in that the phenyluracil 1.1.1 is replaced by the
phenyluracil 1.1.6.
Preference is also given to the compositions 7.1 - 7.173, which differ from the corre-
sponding compositions 1.1 - 1.173 only in that the phenyluracil 1.1.1 is replaced by the
phenyluracil 1.1.7.
Preference is also given to the compositions 8.1 - 8.173, which differ from the corre-
sponding compositions 1.1 - 1.173 only in that the phenyluracil 1.1.1 is replaced by the
phenyluracil 1.1.8.
Preference is also given to the compositions 9.1 - 9.173, which differ from the corre-
sponding compositions 1.1 - 1.173 only in that the phenyluracil 1.1.1 is replaced by the
phenyluracil 1.1.9.
Preference is also given to the compositions 10.1 - 10.173, which differ from the corre-
sponding compositions 1.1 - 1.173 only in that the phenyluracil 1.1.1 is replaced by the
phenyluracil 1.1.10.
Preference is also given to the compositions 11.1 - 11.173, which differ from the corre-
sponding compositions 1.1 - 1.173 only in that the phenyluracil 1.1.1 is replaced by the
phenyluracil 1.1.11.
Preference is also given to the compositions 12.1 - 12.173, which differ from the corre-
sponding compositions 1.1 - 1.173 only in that the phenyluracil 1.1.1 is replaced by the
phenyluracil 1.1.12.
Preference is also given to the compositions 13.1-13.173, which differ from the corre-
sponding compositions 1.1 - 1.173 only in that the phenyluracil 1.1.1 is replaced by the
phenyluracil 1.1.13.
Preference is also given to the compositions 14.1 - 14.173, which differ from the corre-
sponding compositions 1.1 - 1.173 only in that the phenyluracil 1.1.1 is replaced by the
phenyluracil 1.1.14.
Preference is also given to the compositions 15.1 - 15.173, which differ from the corre-
sponding compositions 1.1 - 1.173 only in that the phenyluracil 1.1.1 is replaced by the
phenyluracil 1.1.15.

Preference is also given to the compositions 16.1 - 16.173, which differ from the corre-
sponding compositions 1.1-1.173 only in that the phenyluracil 1.1.1 is replaced by the
phenyluracil 1.1.16.
Preference is also given to the compositions 17.1-17.173, which differ from the corre-
sponding compositions 1.1 - 1.173 only in that the phenyluracil 1.1.1 is replaced by the
phenyluracil 1.1.17.
Preference is also given to the compositions 18.1-18.173, which differ from the corre-
sponding compositions 1.1 - 1.173 only in that the phenyluracil 1.1.1 is replaced by the
phenyluracil 1.1.18.
Preference is also given to the compositions 19.1 - 19.173, which differ from the corre-
sponding compositions 1.1- 1.173 only in that the phenyluracil 1.1.1 is replaced by the
phenyluracil 1.1.19.
Preference is also given to the compositions 20.1 - 20.173, which differ from the corre-
sponding compositions 1.1 - 1.173 only in that the phenyluracil 1.1.1 is replaced by the
phenyluracil 1.1.20.
Preference is also given to the compositions 21.1 - 21.173, which differ from the corre-
sponding compositions 1.1 - 1.173 only in that the phenyluracil 1.1.1 is replaced by the
phenyluracil 1.1.21.
Preference is also given to the compositions 22.1 - 22.173, which differ from the corre-
sponding compositions 1.1 - 1.173 only in that the phenyluracil 1.1.1 is replaced by the
phenyluracil 1.1.22.
Preference is also given to the compositions 23.1 - 23.173, which differ from the corre-
sponding compositions 1.1 - 1.173 only in that the phenyluracil 1.1.1 is replaced by the
phenyluracil 1.1.23.
Preference is also given to the compositions 24.1 - 24.173, which differ from the corre-
sponding compositions 1.1 - 1.173 only in that the phenyluracil 1.1.1 is replaced by the
phenyluracil 1.1.24.
Preference is also given to the compositions 25.1 - 25.173, which differ from the corre-
sponding compositions 1.1 - 1.173 only in that the phenyluracil 1.1.1 is replaced by the
phenyluracil 1.1.25.

Preference is also given to the compositions 26.1 - 26.173, which differ from the corre-
sponding compositions 1.1 - 1.173-only.in that the phenyluracil 1.1.1 is replaced byjie
phenyluracii 1.1.26.
Preference is also given to the compositions 27.1 - 27.173, which differ from the corre-
sponding compositions 1.1-1.173 only in that the phenyluracil 1.1.1 is replaced by the
phenyluracil 1.1.27.
Preference is also given to the compositions 28.1 - 28.173, which differ from the corre-
sponding compositions 1.1 - 1.173 only in that the phenyluracil 1.1.1 is replaced by the
phenyluracil 1.1.28.
Preference is also given to the compositions 29.1 - 29.173, which differ from the corre-
sponding compositions 1.1 - 1.173 only in that the phenyluracil 1.1.1 is replaced by the
phenyluracil 1.1.29.
Preference is also given to the compositions 30.1 - 30.173, which differ from the corre-
sponding compositions 1.1 - 1.173 only in that the phenyluracil 1.1.1 is replaced by the
phenyluracil 1.1.30.
Preference is also given to the compositions 31.1 - 31.173, which differ from the corre-
sponding compositions 1.1 -1.173 only in that the phenyluracil 1.1.1 is replaced by the
phenyluracil 1.1.31.
Preference is also given to the compositions 32.1 - 32.173, which differ from the corre-
sponding compositions 1.1 -1.173 only in that the phenyluracil 1.1.1 is replaced by the
phenyluracil 1.1.32.
Preference is also given to the compositions 33.1 - 33.173, which differ from the corre-
sponding compositions 1.1 -1.173 only in that the phenyluracil 1.1.1 is replaced by the
phenyluracil 1.1.33.
Preference is also given to the compositions 34.1 - 34.173, which differ from the corre-
sponding compositions 1.1 - 1.173 only in that the phenyluracil 1.1.1 is replaced by the
phenyluracil 1.1.34.
Preference Is also given to the compositions 35.1 - 35.173, which differ from the corre-
sponding compositions 1.1 - 1.173 only in that the phenyluracil 1.1.1 is replaced by the
phenyluracil 1.1.35.

Preference is also given to thexornpositions 36.1 - 36.173, which differ from the corre-
sponding compositions 1.1 - 1.173 only in that the phenyiuracil .1.1.1-is replaced by the
phenyluracil 1.1.36.
Preference is also given to the compositions 37.1 - 37.173, which differ from the corre-
sponding compositions 1.1 - 1.173 only in that the phenyluracil 1.1.1 is replaced by the
phenyluracil 1.1.37.
Preference is also given to the compositions 38.1 - 38.173, which differ from the corre-
sponding compositions 1.1 - 1.173 only in that the phenyluracil 1.1.1 is replaced by the
phenyluracil 1.1.38.
Preference is also given to the compositions 39.1 - 39.173, which differ from the corre-
sponding compositions 1.1 - 1.173 only in that the phenyluracil 1.1.1 is replaced by the
phenyluracil 1.1.39.
Preference is also given to the compositions 40.1 - 40.173, which differ from the corre-
sponding compositions 1.1 - 1.173 only in that the phenyluracil 1.1.1 is replaced by the
phenyluracil 1.1.40.
Preference is also given to the compositions 41.1 - 41.173, which differ from the corre-
sponding compositions 1.1-1.173 only in that the phenyluracil 1.1.1 is replaced by the
phenyluracil 1.1.41.
Preference is also given to the compositions 42.1 - 42.173, which differ from the corre-
sponding compositions 1.1 - 1.173 only in that the phenyluracil 1.1.1 is replaced by the
phenyluracil 1.1.42.
Preference is also given to the compositions 43.1 - 43.173, which differ from the corre-
sponding compositions 1.1 - 1.173 only in that the phenyluracil 1.1.1 is replaced by the
phenyluracil 1.1.43.
Preference is also given to the compositions 44.1 - 44.173, which differ from the corre-
sponding compositions 1.1 -1.173 only in that the phenyluracil 1.1.1 is replaced by the
phenyluracil 1.1.44.
Preference is also given to the compositions 45.1 - 45.173, which differ from the corre-
sponding compositions 1.1 -1.173 only in that the phenyluracil 1.1.1 is replaced by the
phenyluracil 1.1.45.

Preference is also given to ther«empositions 46.1 *■ 46.173,-Whicn differ from the corre-
sponding compositions 1.1-1:173 only in that the phenyluracil 1.1.1 is replaced by the
phenyluracil 1.1.46.
Preference is also given to the compositions 47.1 - 47.173, which differ from the corre-
sponding compositions 1.1 - 1.173 only in that the phenyluracil 1.1.1 is replaced by the
phenyluracil 1.1.47.
Preference is also given to the compositions 48.1 - 48.173, which differ from the corre-
sponding compositions 1.1 - 1.173 only in that the phenyluracil 1.1.1 is replaced by the
phenyluracil 1.1.48.
Preference is also given to the compositions 49.1 - 49.173, which differ from the corre-
sponding compositions 1.1 -1.173 only in that the phenyluracil 1.1.1 is replaced by the
phenyluracil 1.1.49.
Preference is also given to the compositions 50.1 - 50.173, which differ from the corre-
sponding compositions 1.1 - 1.173 only in that the phenyluracil 1.1.1 is replaced by the
phenyluracil 1.1.50.
Preference is also given to the compositions 51.1 - 51.173, which differ from the corre-
sponding compositions 1.1 - 1.173 only in that the phenyluracil 1.1.1 is replaced by the
phenyluracil 1.1.51.
Preference is also given to the compositions 52.1 - 52.173, which differ from the corre-
sponding compositions 1.1 - 1.173 only in that the phenyluracil 1.1.1 is replaced by the
phenyluracil 1.1.52.
Preference is also given to the compositions 53.1 - 53.173, which differ from the corre-
sponding compositions 1.1 - 1.173 only in that the phenyluracil 1.1.1 is replaced by the
phenyluracil 1.1.53.
Preference is also given to the compositions 54.1 - 54.173, which differ from the corre-
sponding compositions 1.1 - 1.173 only in that the phenyluracil 1.1.1 is replaced by the
phenyluracil 1.1.54.
Preference is also given to the compositions 55.1 - 55.173, which differ from the corre-
sponding compositions 1.1-1.173 only in that the phenyluracil 1.1.1 is replaced by the
phenyluracil 1.1.55.

Preference is also given to the compositions 56.1 - 56.173, which differ from the corre-
sponding compositions 1.1 -1.173 only in that the phenyluracil 1.1.1 is replaced by the
phenyluracil 1.1.56.
Preference is also given to the compositions 57.1 - 57.173, which differ from the corre-
sponding compositions 1.1 - 1.173 only in that the phenyluracil 1.1.1 is replaced by the
phenyluracil 1.1.57.
Preference is also given to the compositions 58.1 - 58.173, which differ from the corre-
sponding compositions 1.1 - 1.173 only in that the phenyluracil 1.1.1 is replaced by the
phenyluracil 1.1.58.
Preference is also given to the compositions 59.1 - 59.173, which differ from the corre-
sponding compositions 1.1 - 1.173 only in that the phenyluracil 1.1.1 is replaced by the
phenyluracil 1.1.59.
Preference is also given to the compositions 60.1 - 60.173, which differ from the corre-
sponding compositions 1.1 - 1.173 only in that the phenyluracil 1.1.1 is replaced by the
phenyluracil 1.1.60.
Preference is also given to the compositions 61.1 - 61.173, which differ from the corre-
sponding compositions 1.1 - 1.173 only in that the phenyluracil 1.1.1 is replaced by the
phenyluracil 1.1.61.
Preference is also given to the compositions 62.1 - 62.173, which differ from the corre-
sponding compositions 1.1 - 1.173 only in that the phenyluracil 1.1.1 is replaced by the
phenyluracil 1.1.62.
Preference is also given to the compositions 63.1 - 63.173, which differ from the corre-
sponding compositions 1.1 - 1.173 only in that the phenyluracil 1.1.1 is replaced by the
phenyluracil 1.1.63.
Preference is also given to the compositions 64.1 - 64.173, which differ from the corre-
sponding compositions 1.1 - 1.173 only in that the phenyluracil 1.1.1 is replaced by the
phenyluracil 1.1.64.
Preference is also given to the compositions 65.1 - 65.173, which differ from the corre-
sponding compositions 1.1 - 1.173 only in that the phenyluracil 1.1.1 is replaced by the
phenyluracil 1.1.65.

Preference is also given to the compositions 66.1 - 66.173, which differ from the corre-
sponding compositions 1.1 -1.173 only in that the phenyluracU |,1,1 is replacedI by the
phenyluracil 1.1.66.
Preference is also given to the compositions 67.1 - 67.173, which differ from the corre-
sponding compositions 1.1-1.173 only in that the phenyluracil 1.1.1 is replaced by the
phenyluracil 1.1.67.
Preference is also given to the compositions 68.1 - 68.173, which differ from the corre-
sponding compositions 1.1-1.173 only in that the phenyluracil 1.1.1 is replaced by the
phenyluracil 1.1.68.
Preference is also given to the compositions 69.1 - 69.173, which differ from the corre-
sponding compositions 1.1 -1.173 only in that the phenyluracil 1.1.1 is replaced by the
phenyluracil 1.1.69.
Preference is also given to the compositions 70.1 -70.173, which differ from the corre-
sponding compositions 1.1-1.173 only in that the phenyluracil 1.1.1 is replaced by the
phenyluracil 1.1.70.
Preference is also given to the compositions 71.1 - 71.173, which differ from the corre-
sponding compositions 1.1 -1.173 only in that the phenyluracil 1.1.1 is replaced by the
phenyluracil 1.1.71.
Preference is also given to the compositions 72.1 - 72.173, which differ from the corre-
sponding compositions 1.1 -1.173 only in that the phenyluracil 1.1.1 is replaced by the
phenyluracil 1.1.72.
Preference is also given to the compositions 73.1 - 73.173, which differ from the corre-
sponding compositions 1.1 - 1.173 only in that the phenyluracil 1.1.1 is replaced by the
phenyluracil 1.1.73.
Preference is also given to the compositions 74.1 - 74.173, which differ from the corre-
sponding compositions 1.1 -1.173 only in that the phenyluracil 1.1.1 is replaced by the
phenyluracil 1.1.74.
Preference is also given to those compositions, which comprise, as active compound,
the substances listet in one row of table 1 (3-phenyluracil 1.1.1 -1.1.74), and, as further
active compound, the safener N-[[4-[(cyclopropylamino)carbonyl]phenyl]sulfonyl]-2-
methoxybenzamide II, and, as further active compound, 3-{2-chloro-4-fluoro-5-[3-
methyl-2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidin-1-yl]phenoxy}-2-
(ethoxycarbonyl)methoxypyridine.

The weight ratios of the individual-components in the compositions 1.1 to 74,173 are
within the limits stated above, in the case of binary compositions of 3-phenyluracil I and
N-[[4-[(cyclopropylamino)carbonyl]phenyl]sulfonyl]-2-methoxybenzamide li for example
1:1,1:2 or 1:5, and in the case of ternary compositions of 3-phenyluracii I, N-[[4-
[(cyclopropylamino)carbonyl]phenyl]sulfonyl]-2-methoxybenzamide II and herbicide III
for example 1:1:1, 2:1:1, 1:2:1, 1:5:1 or 1:5:2.
In the ready-to-use preparations, i.e. in the compositions according to the invention in
the form of crop protection products, the components I and II and optionally III, in sus-
pended, emulsified or dissolved form, can be present formulated jointly or separately.
The use forms depend entirely on the intended use.
The compositions according to the invention can be applied, for example, in the form of
directly sprayable aqueous solutions, powders, suspensions, also highly-concentrated
aqueous, oily or other suspensions or dispersions, emulsions, oil dispersions, pastes,
dusts, materials for spreading or granules, by means of spraying, atomizing, dusting,
broadcasting or watering. The use forms depend on the intended use; in any case, they
should ensure the finest possible distribution of the active compounds.
Depending on the form in which the ready-to-use preparations are present in the com-
positions according to the invention, they comprise one or more liquid or solid carriers,
if appropriate surfactants and if appropriate further auxiliaries which are customary for
formulating crop protection products. The person skilled in the art is sufficiently familiar
with the recipes for such formulations.
The ready-to-use preparations comprise the components I and II and optionally III and
auxiliaries which are customary for formulating crop protection products, which auxilia-
ries may also comprise a liquid carrier.
Suitable inert additives with carrier function are essentially: mineral oil fractions of me-
dium to high boiling point, such as kerosene and diesel oil, furthermore coal tar oils and
oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, e.g. par-
affins, tetrahydronaphthalene, alkylated naphthalenes and their derivatives, alkylated
benzenes and their derivatives, alcohols such as methanol, ethanol, propanol, butanol
and cyclohexanol, ketones such as cyclohexanone, strongly polar solvents, e.g.
amines such as N-methylpyrrolidone, and water.
Aqueous use forms can be prepared from emulsion concentrates, suspensions, pastes,
wettable powders or water-dispersible granules by adding water. To prepare emul-
sions, pastes or oil dispersions, the active compounds I, II or III, as such or dissolved in
an oil or solvent, can be homogenized in water by means of wetting agent, tackifier,

dispersant or emulsifier. Alternatively, it is possible to prepare concentrates consisting
of active substance, wetting agent,- tackifier, dispersant or emulsifier and, if desired,
solvent or oil, and these concentrates are suitable for dilution with water.
Suitable surfactants are the alkali metal salts, alkaline earth metal salts and ammonium
salts of aromatic sulfonic acids, e.g. ligno-, phenol-, naphthalene- and dibutylnaphtha-
lenesulfonic acid, and of fatty acids, of alkyl- and alkylarylsulfonates, of alkyl sulfates,
lauryl ether sulfates and fatty alcohol sulfates, and salts of sulfated hexa-, hepta- and
octadecanols and of fatty alcohol glycol ethers, condensates of sulfonated naphthalene
and its derivatives with formaldehyde, condensates of naphthalene or of the naphtha-
lenesulfonic acids with phenol and formaldehyde, polyoxyethylene octylphenol ether,
ethoxylated isooctyl-, octyl- or nonylphenol, alkyiphenyl polyglycol ethers, tributylphenyl
polyglycol ether, alkylaryl polyether alcohols, isotridecyl alcohol, fatty alcohol/ethylene
oxide condensates, ethoxylated castor oil, polyoxyethylene alkyl ether or polyoxypro-
pylene alkyl ether, lauryl alcohol polyglycol ether acetate, sorbitol esters, lignosulfite
waste liquors or methylcellulose.
Powders, materials for spreading and dusts can be prepared by mixing or concomitant
grinding of the active substances with a solid carrier.
Granules, e.g. coated granules, impregnated granules and homogeneous granules,
can be prepared by binding the active ingredients to solid carriers. Solid carriers are
mineral earths such as silicas, silica gels, silicates, talc, kaolin, limestone, lime, chalk,
bole, loess, clay, dolomite, diatomaceous earth, calcium sulfate, magnesium sulfate,
magnesium oxide, ground synthetic materials, fertilizers such as ammonium sulfate,
ammonium phosphate, ammonium nitrate, ureas, and products of vegetable origin
such as cereal meal, tree bark meal, wood meal and nutshell meal, cellulose powders,
or other solid carriers.
The concentrations of the active compounds in the ready-to-use preparations can be
varied within wide ranges. In general, the formulations comprise from 0.001 to 98% by
weight, preferably 0.01 to 95% by weight, of active ingredients. The active ingredients
are employed in a purity of from 90% to 100%, preferably 95% to 100% (according to
NMR spectrum).
The compounds according to the invention can, for example, be formulated as follows:
I 20 parts by weight of the active compound composition in question are dissolved
in a composition composed of 80 parts by weight of alkylated benzene, 10 parts
by weight of the adduct of 8 to 10 mol of ethylene oxide to 1 mol of oleic acid N-
monoethanolamide, 5 parts by weight of calcium dodecylbenzenesulfonate and 5
parts by weight of the adduct of 40 mol of ethylene oxide to 1 mol of castor oil.

. Pouring the solution into TOO 000 parts by weight of water and finely distributing it
therein gives an aqueous dispersion which comprises 0.02% by weight of the ac-
tive ingredient.
II 20 parts by weight of the active compound composition in question are dissolved
in a composition composed of 40 parts by weight of cyclohexanone, 30 parts by
weight of isobutanol, 20 parts by weight of the adduct of 7 mol of ethylene oxide
to 1 mol of isooctylphenol and 10 parts by weight of the adduct of 40 mol of eth-
ylene oxide to 1 mol of castor oil. Pouring the solution into 100 000 parts by
weight of water and finely distributing it therein gives an aqueous dispersion
which comprises 0.02% by weight of the active ingredient.
III 20 parts by weight of the active compound composition in question are dissolved
in a composition composed of 25 parts by weight of cyclohexanone, 65 parts by
weight of a mineral oil fraction of boiling point 210 to 280°C and 10 parts by
weight of the adduct of 40 mol of ethylene oxide to 1 mol of castor oil. Pouring the
solution into 100 000 parts by weight of water and finely distributing it therein
gives an aqueous dispersion which comprises 0.02% by weight of the active in-
gredient.
IV 20 parts by weight of the active compound composition in question are mixed
thoroughly with 3 parts by weight of sodium diisobutylnaphthalenesulfonate, 17
parts by weight of the sodium salt of a lignosulfonic acid from a sulfite waste liq-
uor and 60 parts by weight of pulverulent silica gel, and the composition is ground
in a hammer mill. Finely distributing the composition in 20 000 parts by weight of
water gives a spray composition which comprises 0.1% by weight of the active
ingredient.
V 3 parts by weight of the active compound composition in question are mixed with
97 parts by weight of finely divided kaolin. This gives a dust which comprises 3%
by weight of the active ingredient.
VI 20 parts by weight of the active compound composition in question are mixed
intimately with 2 parts by weight of calcium dodecylbenzenesulfonate, 8 parts by
weight of fatty alcohol polyglycol ether, 2 parts by weight of the sodium salt of a
phenol-urea-formaldehyde condensate and 68 parts by weight of a paraffinic min-
eral oil. This gives a stable oily dispersion.
VII 1 part by weight of the active compound composition in question is dissolved in a
composition composed of 70 parts by weight of cyclohexanone, 20 parts by
weight of ethoxylated isooctylphenol and 10 parts by weight of ethoxylated castor
oil. This gives a stable emulsion concentrate.

VIII 1 part by weight of the active compound composition in question.is dissolved in a
composition composed of 80 parts by weight of cyclohexanone and 20 parts by
weight of Wettol® EM 31 (nonionic emulsifier based on ethoxylated castor oil).
This gives a stable emulsion concentrate.
The components I and II and optionally III can be formulated jointly or separately.
The components I and II and optionally III can be applied jointly or separately, simulta-
neously or successively, before, during or after emergence of the plants.
If the active compounds I and II and optionally III are less well tolerated by certain crop
plants, it is possible to use application methods in which the herbicidal compositions
are sprayed with the aid of sprayers in such a way that the leaves of the sensitive crop
plants are as far as possible unaffected, whereas the active compounds reach the
leaves of the undesirable plants growing underneath or the uncovered soil surface
(post-directed, lay-by).
The required application rate of the composition of the pure active compounds, i.e. of I
and II and optionally III without formulation auxiliary, depends on the density of the un-
desired vegetation, on the development stage of the plants, on the climatic conditions
of the location where the composition is used and on the application method. In gen-
eral, the application rate of I and II and optionally III is from 0.001 to 3 kg/ha, preferably
from 0.005 to 2 kg/ha and in particular from 0.01 to 1 kg/ha of active substance.
The required application rates of the 3-phenyluracils I and N-[[4-[(cyclopropylamino)-
carbonyl]phenyl]sulfonyl]-2-methoxybenzamide II are generally in the range from 0.1
g/ha to 1 kg/ha and preferably in the range from 1 g/ha to 500 g/ha or from 5 g/ha to
500 g/ha of active substance.
The compositions are applied to the plants mainly by spraying, in particular foliar spray-
ing. Application can be carried out by customary spraying techniques using, for exam-
ple, water as carrier and spray liquor rates of from about 50 to 1000 l/ha (for example
from 300 to 400 l/ha). Application of the herbicidal compositions by the low-volume and
the ultra-low-volume method is possible, as is their application in the form of micro-
granules.
The compositions according to the present invention are suitable for controlling com-
mon harmful plants in useful plants, in particular in crops such as oat, barley, millet,
com, rice, wheat, sugar cane, cotton, oilseed rape, flax, lentil, sugar beet, tobacco,
sunflowers and soybeans or in perennial crops.

Moreover, it may be useful to apply the compositions according to the invention jointly
as a composition with other crop protection products, for example,with .pestipid.es or'.
agents for controlling phytopathogenic fungi or bacteria. Also of interest is the miscibil-
ity with mineral salt solutions which are employed for treating nutritional and trace ele-
ment deficiencies. Non-phytotoxic oils and oil concentrates may also be added.
The compositions according to the invention can also be used in crop plants which, by
genetic engineering or by breeding, are resistant to one or more herbicides and/ or
fungicides and/or or to attack by insects.
Suitable are for example crop plants preferably corn, wheat, barley, sunflower, rice,
canola, soybeans which are resistant to herbicidal EPSP synthase inhibitors, such as,
for example, glyphosate, to herbicidal glutamine synthase inhibitors, such as, for ex-
ample, glufosinate, to herbicidal protoporphyrinogen-IX oxidase inhibitors, such as, for
example, butafenacil, or to herbicidal ALS inhibitors, such as, for example, imazameth-
abenz, imazamox, imazapic, imazapyr, imazaquin, imazethapyr, or crop plants which,
owing to introduction of the gene for Bt toxin by genetic modification, are resistant to
attack by certain insects.
Surprisingly, the compositions according to the invention which, in addition to the 3-
phenyluracil I and optionally a herbicide III, comprise the safener N-[[4-
[(cyclopropylamino)carbonyl]phenyl]sulfonyl]-2-methoxybenzamide II, are better toler-
ated by useful plants than the respective compositions comprising a 3-phenyluracil I
and optionally a herbicide III without safener II.
The 3-phenyluracils of formula I can be prepared by the preparation processes dis-
closed in WO 01/83459. With respect to the preparation of individual compounds, ref-
erence is made to the examples of WO 01/83459. Compounds, which are not explicitly
disclosed in this document, can be prepared in an analogous manner.
N-[[4-[(cyclopropylamino)carbonyl]phenyl]sulfonyl]-2-methoxybenzamide II can be pre-
pared by the preparation processes disclosed by the earlier applications WO 99/16744
and WO 05/00797.
Use Examples
The effect of the herbicidal compositions according to the invention of components I
and II and, if appropriate, III on the growth of undesirable plants compared to the herbi-
cidally active compounds alone can be demonstrated by the following greenhouse ex-
periments.
For the pre-emergence treatment, directly after sowing the active compounds, which
had been suspended or emulsified in water, were applied by means of finely distributed

nozzles. The containers were irrigated gently to promote germination anC1-Tjrowth and
subsequently covered with transparent plastic hoods until plant had rooted. This cover ...
caused uniform germination of the tests plants, unless this was adversely affected by
active compounds.
For the post-emergence treatment, the test plants were first grown to a height of 3 to
20 cm, depending on the plant habit, and only then treated. Here, the herbicidal com-
positions were suspended or emulsified in water as distribution medium and sprayed
using finely distributing nozzles.
The respective component I was formulated as a 12% by weight strength emulsion
concentrate, and component II as a 10% by weight suspension concentrate. Optionally
components III can be used in their appropriate available formulation types.
The components I, II and optionally III were introduced to the spray liquid with the
amount of solvent system used for applying the active compound.
The test period extended over 21 days. During this time, the plants were tended, and
their response to the treatments with active compound was evaluated.
The evaluation for the damage caused by the chemical compositions was carried out
using a scale from 0 to 100%, compared to the untreated control plants. Here, 0 means
no damage and 100 means complete destruction of the plants.
A safener action is present if the damage to the crop plant caused by a mixture accorC1-
ing to the present invention which contains N-[[4-[(cyclopropylamino)carbonyl]phenyl]-
sulfonyl]-2-methoxybenzamide is less than the damage caused when the phenyluracil I
optionally in mixture with a herbicide III according to the present invention is used with-
out N-[[4-[(cyclopropylamino)carbonyl]phenyl]sulfonyl]-2-methoxybenzamide.

Example 1: Herbicidal action of the post-emergence applied mixture of 3-pheny|uracil
1.1.7 and N-[[4-[(cyclopropylamino)carbonyl]phenyl]sulfonyl]-2-methoxybenzamide II
against POLCO, CHEAL, ABUTH and AMARE and safener action with regard to
TRZAS, HORVW and ZEAMX

The safener N-[[4-[(cyclopropylamino)carbonyl]phenyl]sulfonyl]-2-methoxybenzamide II
has not shown damaging effect on TRZAS, HORVW and ZEAMX and has not shown
herbicidal acitivity on POLCO, CHEAL, ABUTH and AMARE at application rates of 150
g/ha applied post-emergence.

We claim:
1. A composition comprising 3-phenyluracils I

wherein the variables R1 to R7 are as defined below:
R1 is methyl or NH2;
R2 is C1-C2-haloalkyl;
R3 is hydrogen or halogen;
R4 is halogen or cyano;
R5 is hydrogen or C1-C6-alkyl;
R6, R7independently of one another are hydrogen, C1-C6-alkyl, C1-C6-alkoxy,
C3-C6-alkenyl, C3-C6-alkynyl, C3-C7-cycloalkyl, C3-C7-cycloalkenyl,
phenyl or benzyl;
including their agriculturally acceptable salts; and
N-[[4-[(cyclopropylamino)carbonyl]phenyl]sulfonyl]-2-methoxybenzamide II

including their agriculturally acceptable salts and, provided they have a carboxyl
group, their agriculturally acceptable derivatives.
2. A composition as claimed in claim 1 wherein the variables R1 to R7 in formula I
are as defined below:
R1 is methyl or NH2;
R2 is trifluoromethyl;
R3 is hydrogen, fluorine or chlorine;
R4 is halogen or cyano;
R5 is hydrogen;
R6, R7 independently of one another are hydrogen, C1-C6-alkyl, C3-C6-alkenyl,
C3-C6-alkynyl, C3-C7-cycloalkyl, C3-C7-cycloalkenyl, phenyl or benzyl.
3. A composition as claimed in claim 1 or 2, wherein R6 and R7 in formula I are
identical or different C1-C6-alkyl radicals.
4. A composition as claimed in claim 1, wherein the variables R1 to R7 in formula I
have the following meanings:
R1 is methyl;
R2 is trifluoromethyl;
R3 is fluorine;
R4 is chlorine;
R5 is hydrogen;
R6, R7 independently of one another are C1-C6-alkyl.
5. A composition as claimed in claim 1, wherein the 3-phenyluracil I is 3-
phenyluracil 1.1.7, where R1 is methyl, R6 is methyl and R7 is isopropyl.
6. A composition as claimed in any one of claims 1 to 5 comprising as the only herb-
icidal active compound a 3-phenyluracil I in combination with the safener N-[[4-
[(cyclopropylamino)carbonyl]phenyl]sulfonyl]-2-methoxybenzamide II.
7. A composition as claimed in any one of claims 1 to 5 comprising a 3-phenyluracil
I, N-[[4-[(cyclopropylamino)carbonyl]phenyl]sulfonyll-2-methoxybenzamide II and
at least one herbicide III selected from the classes III.1) to III.15.
8. A composition as claimed in any one of claims 1 to 5 and 7 wherein the herbi-
cides III are selected from the following classes III.1) to III.15):
III.1) from the group of the lipid biosynthesis inhibitors:
clodinafop, cyhalofop, diclofop, fenoxaprop, fenoxaprop-p, fluazifop, fluazi-
fop-P, haloxyfop, haloxyfop-P, metamifop, quizalofop, quizalofop-P, al-
loxydim, butroxydim, clethodim, cloproxydim, cycloxydim, profoxydim,
setnoxydim, tepraloxydim, tralkoxydim and pinoxaden;
III.2) from the group of the ALS inhibitors:
amidosulfuron, bensulfuron, chlorimuron, chlorsulfuron, cyclosulfamuron,
flupyrsulfuron, foramsulfuron, halosulfuron, imazosulfuron, iodosulfuron,
mesosulfuron, metsulfuron, nicosulfuron, oxasulfuron, primisulfuron, pro-
sulfuron, pyrazosulfuron, rimsulfuron, sulfometuron, sulfosulfuron, thifen-
sulfuron, tnasulfuron, tribenuron, trifloxysulfuron, triflusulfuron, tritosulfur-
on, imazamox, imazapic, imazapyr, imazaquin, imazethapyr, cloransu-
lam, diclosulam, florasulam, flumetsulam, metosulam, penoxsulam,
bispyribac, pyriminobac, propoxycarbazone, flucarbazone, pyribenzoxim,
pyriftalid, pynthiobac, flucetosulfuron, orthosulfamuron, pyrimisulfan and
[N-(5,7-dimethoxy[1,2,4]triazolo[1,5-a]pyrimidin-2-yl-2-methoxy-4-(tri-
Tluormethyl)-3-pyridinesulfonamide;
III.3) from the group of the photosynthesis inhibitors:
atrazine, cyanazine, simazine, terbuthylazine, metamitron, metribuzin,
chloridazon, amicarbazone, chlorotoluron, diuron, isoproturon,

methabenzthiazuron, bentazone, propanil, bromoxynil, ioxynil and
paraquat;
III.5) from the group of the bleacher herbicides:
norflurazon, diflufenican, picolinafen, beflubutamid, mesotrione, sulcotri-
one, isoxaflutole, benzofenap, pyrazolynate, pyrazoxyfen, benzobicyc-
lon, 4-(3-trifluoromethylphenoxy)-2-(4-trifluoromethylphenyl)pyrimidine,
topramezone, 4-hydroxy-3-{[2-methyl-6-(trifluoromethyl)-3-pyridinyl]car-
bonyl}bicyclo[3.2.1 ]oct-3-en-2-one, 4-hydroxy-3-{[2-(2-
methoxyethoxy)methyl-6-(trifluoro-methyl)-3-
pyridinyl]carbonyl}bicylo[3.2.1 ]oct-3-en-2-one, 4-hydroxy-3-[4-(methyl-
sulfonyl)-2-nitrobenzoyl]bicyclo[3.2.1]-oct-3-en-2-one, 2-[2-chloro-4-
(methylsulfonyl)-3-[(2,2,2-trifluoroethoxy)methyl]benzoyl]-3-hydroxy-2-
cyclohexen-1-one and pyrasulfotole;
III.6) from the group of the EPSP synthase inhibitors:
glyphosate;
III.7) from the group of the glutamine synthase inhibitors:
glufosinate;
III.9) from the group of the mitose inhibitors:
oryzalin, pendimethalin and trifluralin;
III.10) from the group of the VLCFA inhibitors:
acetochlor, butachlor, dimethenamid, dimethenamiC1-P, metazachlor,
metolachlor, S-metolachlor, pethoxamid, pretilachlor, flufenacet, mefen-
acet, fentrazamide, cafenstrole and indanofan;
III.13) from the group of the auxin herbicides:
2,4-D, dichlorprop, dichlorprop-P, mecoprop, MCPA, mecoprop-P, dic-
amba, quinclorac, quinmerac, clopyralid, fluroxypyr, picloram, triclopyr
and aminopyralid;
III.14) from the group of the auxin transport inhibitors:
diflufenzopyr;
III.15) cinmethylin, oxaziclomefone and triaziflam;
and the agriculturally acceptable salts and, provided they have a carboxyl group,
the agriculturally acceptable derivatives thereof.
9. A composition as claimed in any one of claims 1 to 8 in form of a crop protection
composition comprising additionally at least one inert liquid and/or solid carrier, if
desired at least one or more surfactants and, if appropriate, at least one or more
further auxiliaries.

ABSTRACT

HERBICIDAL COMPOSITIONS BASED ON 3-PHENYLURACILS
AND N-[[4-[(CYCLOPROPYLAMINO)-CARBONYL]PHENYL]SULFONYL]
-2-METHOXYBENZAMIDE
A herbicidal composition comprising 3-phenyluracils I

wherein R1 to R7 are as defined in the specification and
N-[[4-[(cyclopropylamino)carbonyl]phenyl]sulfonyl]-2-methoxybenzamide II

and optionally at least one herbicide selected from a group as defined in the specification.